Sodium Bicarbonate → Ethyl N-((5-methyl-2-(isopropyl)cyclohexyl)carbonyl)glycinate

HRID 1447837Notes

Reaction equation

HRID 1447837 reaction equation
C(=O)(O)[O-].[Na+].Cl.[CH2:7]([O:9][C:10](=[O:13])[CH2:11][NH2:12])[CH3:8].[CH:14]1([CH3:26])[CH2:19][CH2:18][CH:17]([CH:20]([CH3:22])[CH3:21])[CH:16]([C:23](Cl)=[O:24])[CH2:15]1>O.CCOCC>[CH2:7]([O:9][C:10](=[O:13])[CH2:11][NH:12][C:23]([CH:16]1[CH:17]([CH:20]([CH3:22])[CH3:21])[CH2:18][CH2:19][CH:14]([CH3:26])[CH2:15]1)=[O:24])[CH3:8]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 11521869Ethyl N-((5-methyl-2-(isopropyl)cyclohexyl)carbonyl)glycinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium bicarbonate (8.4 g., 0.1 mole) and glycine ethyl ester hydrochloride (7 g. 0.05 mole) were dissolved in water (100 ml.), and a solution of p-menth-3-oyl chloride (10 g., 0.05 mole) in ether (50 ml.) was added and the mixture stirred vigorously at room temperature for 2 hours. At the end of this time the other layer was separated and dried (MgSO4). Removal of the solvent left an oily solid (12.3 g.) This was distilled under reduced pressure to yield N-p-menth-3-oylglycine ethyl ester, bp. 150°-2°/0.1 mm. as a colourless liquid which rapidly solidified.

Workup

  1. customAt the end of this time the other layer was separated
  2. dry with materialdried (MgSO4)
  3. customRemoval of the solvent
  4. waitleft an oily solid (12.3 g.)
  5. distillationThis was distilled under reduced pressure

Sources & evidence

ORD record
ord-f45ebdff6e5e467d809c71f33ce6b545
Source dataset
uspto-grants-1979_12
Patent number
US04178459

Reaction notes

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